I remember when José Mourinho took over as Chelsea’s manager in 2004 - he brought in raw ambition and a style of leadership that was revolutionary for me. He is the first person I saw who was not apologetic about his ambitions. 

But let me take a step back and tell you about football, Chelsea, and how I became a fan of José Mourinho.     

Growing up in a cricket-mad nation, it is something of a wonder that I got into football. Don’t get me wrong, I love cricket too and play it regularly, but I have a special connection with football. I have been playing the beautiful game right from my school days, but for those who know me well, Chelsea is what they associate with football and me. 

I became a Chelsea fan by happenstance. When I was in school and even in college, the English Premier league was not all that popular in India, at least not like it is now. And, the few Indian fans were mostly followers of Man U and Liverpool. But, I had a coach who was from West London and was a Chelsea fan, and that’s how I heard of the club for the first time and started following it.

In the 1990s, Chelsea was not one of the bigger clubs; legacy clubs like Liverpool and Manchester United were the behemoths of English club football. It was late to the party, but by early-2000s started dominating. PSG and Manchester City today are just following the playbook created by Chelsea. Many will attribute the change of fortunes of Chelsea to Roman Abramovich, the billionaire Russian oligarch who bought the club in 2003. For me personally, it was the manager that Abramovich brought on board in 2004 that cemented my love for Chelsea.

When José Mourinho moved from Porto to Chelsea in 2004, he brought raw ambition to the Club. What I admire the most about him is his genius at mind games. He would make controversial statements to the media, like calling himself “special one”, to ensure the pressure stayed on him, and away from his players. And what rich dividends did he, the club, the players, and us fans reap - winning back-to-back league cups and championships. 

While 2008 was not a particularly great season for Chelsea, it was a special one for me because I got to watch Chelsea play in-person for the first time ever. It was Girish Mathrubootham, who was my manager in Zoho at that time, who took me to the game. There, Girish and I clicked a pic in front of the poster of legendary player John Terry, and 10 years later we were able to click a pic with the man himself when we invited him to be the keynote speaker at a Freshworks event. It was an unbelievable experience. 

With John Terry and Girish Mathrubootham at a Freshworks event

Something Terry mentioned then stood out for me. He spoke about Mourinho’s dedication. Many know about his flamboyance and the controversial statements he made to the press, but they don’t know how he worked with his players. Terry said Mourinho was always the first person on the ground for practice and would be there before the players would get there. He recalled how he tried to be the first person to get to the ground, but Mourinho beat him to it every single time.

For me this is one of the central tenets of effective leadership - walking the talk.

Let me dive in a bit to what I believe are the key tenets of Mourinho’s leadership style, and what we can learn from him as founders and leaders.

Assertive: Mourinho is known for his plain-speaking and truth telling. He doesn’t mince words or sugarcoat. He is assertive about expectations and challenges. He is also exuberant in his appreciation, as most know from his on-field celebrations. He does get confrontational and does get into controversies, but we should be choosing the parts we want to emulate, right?

Demanding: He is a demanding manager. He expects his players to always perform at their best, every time. He is not just all noise. Behind the scenes, he worked hard with his players at Chelsea to ensure they were world beaters. And, as I mentioned earlier, he worked as hard alongside his team.

Results-oriented: He is laser-focused on results. Mourinho has always made it clear he is in it to win, and the hard work matters only if they win. This focus ensures efforts are always channeled in the right direction and efforts don’t get wasted. 

Strategic: Mourinho is a master at mind games and in understanding the opposition’s weakness and attacking it. He knows what battles to pick, and where to focus his energies. This is particularly useful for founders, because there are so many things that demand our attention we may pick up too many problems to focus on. This can be counter-productive..

Decisive: Mourinho is known for his quick decision-making. There is nothing slow about him. He is also action-oriented, making bold changes when needed.

Inspiring: Mourinho is considered a task master, and yet his players are extremely loyal to him. When he was let go by Chelsea, many of the club’s top players were distraught and were ready to follow him. His ability to motivate and inspire his team is what made him a great manager, not just a good one. 

Mourinho is a great example of how a leader of a team filled with superstars needs to lead, and all of us, startup founders, can learn a lesson or two from him.